1: 79 percent / tetrahydrofuran / 8 h / Heating 2: 100 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 3 h / Ambient temperature 3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 48 percent / Cs2CO3 / dimethylformamide / 16 h / 760 Torr / Ambient temperature 5: 90 percent / H2, Et3N / 10 percent Pd/C / acetonitrile; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 1 h / 0 °C 2: H2 / 10percent Pd/C / ethanol / 18 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / -5 °C 4: NaI / acetone / 2 h / Heating 5: 75 percent / K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 1 h / 0 °C 2: H2 / 10percent Pd/C / ethanol / 18 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / -5 °C 4: NaI / acetone / 2 h / Heating View Scheme

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 1 h / 0 °C 2: H2 / 10percent Pd/C / ethanol / 18 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / -5 °C 4: NaI / acetone / 2 h / Heating 5: 59 percent / K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) THF 2: H2 / Pd-C / ethanol 3: 92 percent / NEt3 / CH2Cl2 4: 71 percent / hydrazine hydrate / aq. ethanol 5: 65 percent / CH2Cl2 6: KOt-Bu / 2-methyl-propan-2-ol / Heating 7: 80 percent HOAc / Heating View Scheme

pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride in dichloromethane

pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane T=0°C; 1 h;

in pyridine

1: pyridine / CH2Cl2 / 8 h / 20 °C 2: NaH / dimethylformamide / 3 h / 20 °C 3: H2 / 10 percent Pd/C / ethanol / 96 h View Scheme

sodium hydroxide in water